


Disrobed

by SoundofSilence



Category: Supernatural
Genre: Billionaire Castiel, Destiel - Freeform, F/F, F/M, M/M, Masturbation, Mutual Masturbation, My First Destiel Fanfic, Objectification, Older Castiel, Older Man/Younger Man, Older Man/Younger Woman, Sex Worker Charlie, Sex Worker Dean, Slut Shaming, Stripper Charlie, Stripper Dean, Stripping, Teen Charlie, Teen Dean, Teen Dean Winchester
Language: English
Status: In-Progress
Published: 2015-07-03
Updated: 2017-11-21
Packaged: 2018-04-07 12:02:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 14,182
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4262559
Author URL: https://archiveofourown.org/users/SoundofSilence/pseuds/SoundofSilence
Summary: <blockquote class="userstuff">
              <p>18 year old Dean Winchester is on his own in NYC for the first time and he's finding out how expensive the city can be. Desperate to make his rent he lets a friend talk him into answering a newspaper ad. It's wild, even for Dean. Promises easy money for good looking young men to participate in private shows hosted in the penthouse of a secretive and mysterious billionaire.</p>
            </blockquote>





	1. The City

**Author's Note:**

> This is my very first published Destiel smut fanfic and I'm really nervous about putting my work out there, I hope you like it! This fic is AU in that Dean and Charlie are both 18. Everyone depicted in this fic is 18 years old or older unless specified.
> 
> NOTE: Smutt shows up in Chapter 6. ;)

It's cold, here. Not the kind of cold Dean's used to. The city is bitter, damp and he feels the chill of it in the marrow of his bones. He's in dark layers, his coat, sweater, beanie. Doesn't even look like himself these days, but then he's kind of not himself.

Dean's out on his own for the first time in his life. No dad, no Sam and no Impala and while the former, the lack of family, leaves a sort of dull ache somewhere in his chest? It's the latter that's got him destination-bound in mass transit, standing in front of the door with his personal brand of comfort blasting through cheap headphones. Holding on to the rail and the seat beside him, swaying a bit as the train meets it's destination.

The doors open and Dean finds himself pushing through the small crush of commuters heading home after a long day. His own trek is quick, he has a routine. Out of the stations, up to the street and straight for a sandwich shop where he still has a little good credit. They know he's coming, the BLT he orders every day is wrapped in white paper and waiting for him to swing by the counter and pick it up. Good credit - they know he can't pay them back and Dean knows they know. Every day he gets a smile from the girl behind the counter. If the owner's in he gets a pat on the back, 'Look at this boy! What a boy!' Pride from a man he's only known for three months that his own father couldn't muster.

And he's lonely.

He's on the fourth floor of a building that would scare the ghost from Dark Water. There's an elevator but it's broken, they keep chairs in it. The steps up to his apartment are, for some stupid reason, about half as wide as they should be. Dean's down his hall and pushed through his apartment door and no sooner does he have his coat off, tossing it on the shitty, threadbare love seat than he's startled by a hollow thump somewhere behind him.

_Knock. Knock. **Knock.**_

It's too early in the week for the rent and a visitor at this hour of the morning is weird, even by Dean's standards. Still, he makes his way to the door, lines an eye up with the peephole and sighs, weakly.

Sure, he's lonely. But Dean isn't exactly on his own. Sure, the trio of his surviving family has gone their separate ways, Sam to college and John fighting the good fight. That doesn't mean Dean is alone in the world. Charlie, the quick witted redhead in the apartment across the hall that now grins at him from the other side of his door, had run into him the day he moved into his building and they hit it off pretty quick.

" _I'm not home_." He almost yawns, opening the locks and tugging the door open. Dean leans on the wall and half closes his eyes for a moment, "What? God, Charlie. It's like six in the a.m., don't you _ever_ _sleep_?"

She's smiling, nervously so. Obviously trying to come up with a great pitch for whatever she's about to ask and Dean can't bring himself to wait patiently. He makes a 'get on with it' gesture in the air and Charlie sighes, winces, "I need fifteen dollars." Dean groans at that, heads into the apartment and leaves Charlie standing in the open door. Which, of course, she takes to be an invitation to follow, "Only until Monday! _Swear_ , I can give you twenty on Monday."

"Dude, you owe me _fifty-eight_ already. Look, I would but I'm tapped. Only so much blood you can give before they're on to your ass." They make it to the dining room table, a small card table in the corner of the living room over a mini fridge and wearing a coffee maker. He's making coffee almost as soon as Charlie invites herself to sit, "What's the fifteen for?"

"Would you believe..." Charlie's trying, Dean's got to give her that, "A _birthday cake_?"

Dean snorts, sits across from her, "Is it for a birthday cake?"

She winces, tries to smile and make it comical, "No?"

"Yeah, alright. What's up?" Sighing, "Level with me, Kiddo."

And Charlie gives in, slumps back in her seat and stretches her arms out onto the table in front of her, "I'm _beyond_ passed due with my rent, that's what's up. The lights are out unless I can make the money by _Friday._ "

"Oh, _man_..." Dean scratches his ear, sits himself back and drapes an arm over the back of the folding chair next to him. Suddenly his tight belt seems like it could give a bit to help out a friend, " _Fifteen bucks,_ eh?"

She shrugs, it's weak, "Forty-five but I figured fifteen was a place to start."

"Great. So what's all this crap about hittin' me back with twenty on Monday? _What happens Monday_?"

Charlie finally stands and starts to slowly wander to the love seat, slumping on it, "It sounded close but still plausible? Ugh... I'm _kinda_ running out of options. I haven't had a paycheck since January. Dean, if I don't find something soon..."

"Right." And he's up, too, pushing out of the chair to meet her. He takes a seat on the crate board coffee table in front of Charlie, elbows resting on his knees, "Hey, I get ya. I'm in the same boat. But there's nada, zip. Even the unemployment office? Nothing. I'm startin' to get desperate, here. But, hell. There's gotta be something, right? Just got to figure out what our options are."

"Well, _actually.._." Charlie seems a little nervous now, fishing in her jacket pocket until she finds a folded piece of newspaper. She opens it up, smooths it on her knee and starts to hold it out to Dean. When he reaches for it, though, she stops him, "You have to _promise_ not to laugh."

"Oh, please. Just gimme the -"

" _Promise_."

Dean's rolling his eyes, sighing and then, finally, nodding, "Give it here." he takes the paper from her and turns it right-side up, looking it over with a little bit of a scowl. He's seen these ads before, every week in the want ads section of the free press paper that gets slipped under his door on Sundays.

_**Nude Models Wanted for Private Shows and Parties** _

_Are you a hot, healthy and outgoing individual between_  
_the ages of 18 and 25 who wants to earn some fast cash_  
_while attending New York's wildest upscale parties? Are_  
_you interested in meeting new people? Do you love to_  
_feel sexy and be the center of attention? CE Parties are what_  
_you've been waiting for! Call to set up an interview, we_  
_want to hear from you! Drug and STD testing is mandatory._  
_Candidates of all genders welcome. Celestial Entertainment_  
_is an equal opportunity employer. Must be 18 years old or older_  
_and a legal resident of the United States with valid I.D._  
_or driver's license. Transportation is provided for those who_  
_qualify._

"Oh, _come **on**_ , Charlie... you gotta be kiddin' me."

"Well, what _else am_ I supposed to do?" Charlie folds her arms at her waist, rests her head back on the cushion behind her and lets her eyes snap shut, "Argh, I'm running out of stuff. You said we had to find out options... well, _this is an option_ , Smartass."

"Yeah, no it ain't." Dean starts crumpling the paper, rolling it into a ball between his palms, "Dude, _anything_ else... those places, man. You're asking for trouble. Besides, you ever even _stripped_ before?"

"Um, **excuse you**." She reaches forward, snatching the little ball of newspaper out of Dean's hands, "I take my clothes off _every morning_ and _every night_. How hard could it really be?" Charlie unrolls it, starts to smooth it out over her knee again, "Whatever, forget it. I'll figure something else out."

" _Hey_ ," His hand finds both of hers, rests atop, "We'll find something. I know it."

"I know. I just... I hope it's soon."


	2. Party Girl

**Notes for the Chapter:**

> This chapter contains mild slut shaming. It's not right, it's not cool and I try to make that clear in the story but some people might be sensitive to it. It's part of the story but that doesn't mean I condone it!

The next six days sees Dean walking through life like a zombie, doing shifts at a local laundry that are practically charity for how little they pay him and picking up some work as day labor in the garden of a big, old house who's tenant he's never met. But he likes the other guys on the job and money is money. Still, he's killing himself and the wage is nothing to write home about.

When he finally makes it to the lobby of his building he's confronted with two things he really doesn't need today. Firstly, dubstep somewhere in the building and it's loud. So he's not foreseeing a good night's sleep. The second being his balding, middle-aged landlord, Mr. Brijesh, practically in his face the second he walks through the doors, "Well, hey there. If it ain't my old pal Sambora, how the hell are ya Sambora? Ya look good." his arm circles Dean's shoulders, hooking over behind his neck and pulling him down to his landlord's level. Boy, he does not look or sound happy, "I _bet_ you don't know what day is today? _Go ahead_ , tell me **what day** is today."

Dean winces, hunches and lets himself be walked towards the staircase. He has one eye closed, trying to think, "Uh... _garbage day_? It's garbage day, right? Oh, dude, no wait... is it our _anniversary already_?"

Brijesh tightens his grip on Dean who makes a quick, quiet, 'Agh!', "Funny. _**Fun**_ _-ny_. You're hilarious." And it's really not possible to do what they're doing, trudge up those narrow stairs, side by side, one man having the other in a really fake looking headlock, "It's _Tuesday_ and that means you're overdue with your rent. Do you want me to sing the ' _pack your shit and move_ ' song? I added a verse since last time."

"Hey," It takes all four flights for Brijesh to turn Dean loose and, when he does, Dean immediately fixes his hair, "I'm good for it. I mean, heck, when have I ever kept you waiting?"

"Do you really want me to answer that?"

And Dean's sighing, unlocking his apartment door, "I got a hundred n' seventy-five, that tide you over, Sharky?"

Brijesh has his hands on his hips and is about to answer when Charlie's door swings open and the dubstep Dean heard earlier suddenly booms out into the hallway. When she staggers out into the hallway wearing a grin and what looks like neon Geisha makeup, her name is called by at least two voices inside the apartment, an apartment that's apparently the place to be tonight judging by the gleeful crowd inside.

Now Dean's got a look on his face that says his anxiety has just skyrocketed while, beside him, their landlord is having a silent meltdown, "What is all this!? You can't do this!"

But Charlie ignores him, grinning and a little stoned, "What's up, Bitches!"

Dean winces and Brijesh sidelines to him, "Did she just call me a bitch?" He doesn't wait for an answer but dives right in with Charlie again, "You can't go around calling people bitches, Bradbury. Especially when you owe them money, _moolah_ , scratch. You're three weeks past due and guess what? You're _outta_ here!"

"Oh, _pfft_." It looks like Charlie but the sound it's making just confuses Dean, who's now trying every key on his ring to get into that apartment. Charlie puts an arm around Dean, the other around Brijesh, "You little, _little_ man." She lets them go so that she can reach into the pocket of her harem pants an pull out an outstanding wad of cash, "I have your money." She counts a bill out at a time, measured with her words, "All. Your. Money." and peels it off the roll, literally slapping it into Brijesh's chest. Then comes another wad counted off the roll and another slap, "And that's for Dean. Are we done here?"

By now the landlord has stopped paying attention to anything but the money in his hands, his entire demeanor is softer and friendlier and when Charlie asks if they're 'done here', all she gets in response is a giddy salute as he wanders off to the stair well.

Dean watches Brijesh go, unable to get his head around it all, "What just happened?"

"Nothing," Charlie beams, "You're just looking at an _independent woman_ , my friend, that's all."

"What? _How_?"

She knew he was going to ask and already had the newspaper clipping out of her pocket, held up with two fingers, "Remember that _thing_ you told me not to do?"

"Oh, man..." Dean takes it from her. Swipes, actually, looking at the paper in mild horror, "Oh man, tell me you didn't..."

"I **did**. And, guess what? It was great! I mean, it was a little scary at first but you should see some of these parties. And everybody's so, I dunno. Professional?"

" _God_ _ **damn**_ _it_ , Charlie..." Dean sighs rough, leans back against the door frame and facepalms right into the newspaper clipping, "But you're okay, right? Nobody did anything weird to ya, you're good?"

"I'm _better_ than good. Two parties and I'm set until July, Dean, two parties! They invited me back for more. All I had to do was go to the party, mingle-"

" _Naked_?" Yeah, Dean's picturing it. Sue him.

She laughs it off, "No, actually they have a wardrobe thing. It's complicated. You don't take off your clothes until..."

"Until?" Still picturing it.

"Well," and now Charlie's not sure what to say because she knows how protective Dean is of his people, "The parties are thrown by these... guys."

"Whoa, wait. What kinda 'guys' are we talkin', here?"

Sighing, she shrugs, folds her arms and leans against the wall next to Dean, "Actors, politicians, CEOs. Billionaires who can afford it. Anyway, they throw a party and hire these Dolls, that's what they called us and you just go in and do hair and makeup, you know, weird stuff. And then they send you to this party and you just have a good time and get paid for it. Two hundred bucks just to drink their champagne, nobody hassling you over an I.D. - how cool is that?"

"Yeah, you're leaving crap out Charlie. What you shoved in Brijie's face weren't no _two hundred_ bucks."

"About that. Can we... _go inside_?"

Dean doesn't look thrilled with that answer. Concern pitches his brows but he does as she asks, finally opens the door and the two go inside. He tosses the keys on the card table and takes a seat, "Okay."

Charlie's hands worry against each other and she slowly sinks to the chair across from Dean, " _Okay_ ," is echoed but she doesn't seem to realize she said it. She swallows a lump in her throat and takes a breath, "Well, if you go to these parties you're going there to be... variety. Like a buffet. And if one of the guys who threw the party likes what they see, that's when they take you to the _bedroom._.. that's where the real money is."

"Oh god... _oh god_ , Charlie..."

"No, it's not that, that's... that's just what they call it. I think they like trashy names for things. Nobody touched me. Actually, they make you sign this _thing_ that says what you will and won't do and if you let them touch... you can make more money but I couldn't. Don't worry. No one made me feel stupid or bad for it. Anyway, you go inside this room and it's all dark and there's a spotlight, sometimes a bed... and, well. You pose."

" _Pose_..." Dean does not like the sound of that but, again, he can't help picturing it.

" _Pose_. The guy who you're there to entertain," Charlie doesn't mean for this to sound so violating but it does, "He writes this number down on a piece of paper and if you agree to the money then you wait for him to tell you to disrobe and you... pose. The way he tells you to." She can see the look of disbelief in Dean's eyes and sighs, getting to her feet. She paces slowly towards the window, rubbing at her thighs in a nervous tick, "I didn't do anything wrong."

"Who you tryin' to convince there, Chuck? Me or you?"

Which is obviously the wrong thing for Dean to say because Charlie turns on him, angry, "So, what Dean? I just let myself get evicted? I just search and search for a job that doesn't exist and starve while I do it? You know, I don't have to answer to you or explain myself, I'm a grown woman."

"Yeah, well." Dean's sounding judgmental, boy is he ever, but he can't seem to stop himself, "You're _acting like_ a frickin' kid. You don't want me lookin' out for you? _Too bad_ , baby, you got me."

"Looking out for me?" She tries to laugh but it comes out angry, " _You're_ looking out for ** _me_**? You can't even feed yourself, Dean! I just kept you from getting evicted!" and she's headed for the door, beyond tired of his bullshit and wanting out, wanting to enjoy her party and her hard earned money, "If you weren't so proud you'd be down there tonight doing the same thing instead of sitting up here judging me. You know what? It is a shitty way to earn a living but nobody _there_ made me feel like a slut for doing it, that was _my best friend's job_. I'm outie." The door is hauled open and Charlie barks before it slams behind her, "You're welcome about the rent, Dickface!"


	3. Making Up

When Charlie opens her door in the morning she doesn't expect to find Dean there with Chinese food. She's never met Sam but she's pretty sure the look Dean is giving her right now is the famous Winchester 'puppy dog' look she's heard so much about. She takes in a breath and sighs it out, knowing this is his 'says sorry' and he has a hard time putting it into words, "Come on, we'll do your place. Not... everybody went home last night, so yeah."

Dean just looks relieved and nods, in no mood to wake up the half-naked rave hippies he can see sprawled out on Charlie's furniture in the background. They move quickly through the hall and slip into Dean's apartment and, as soon as the takeout is set down, Charlie's already sitting at the table, digging in. Dean leans under the table to grab a couple of Cokes out of the mini fridge and sets Charlie's in front of hers.

She smirks at him, quirks a brow and nods at the bottle of soda that would normally be a beer, "They're on to you at the mart already?"

"Whoa, hey. Maybe I just like Coke, ah?" He goes to take a swig of his but stops short, pauses and finally, "Look, about last night..."

"It's okay. Well, it's not okay okay but I know you didn't mean it."

"Just twigged me, that's all." He sighs, sets his drink down, "I worry about you, kid."

"I can take care of myself, Dean."

"Yeah I know it. Boy do I ever know it but that's not gonna stop me worrying. I just should'a never said... yeah."

"Well, yeah." She laughs and rests her hand on his wrist, "I'm good, Dean. It's nice to not worry. I'm going back tonight, I wish you'd come with me. Two hundred just to drink their booze and eat their food, you don't have to do anything else. Plus you check the place out and give it the Winchester seal of approval if it's really bugging you."

And, man, he wishes he had an argument for that. But she's right, he can use a night off with pay, free drinks and a hope that they won't card him and he really wants to see if this place is as bad as he thinks it is, "Hell, why not? You're gonna walk into the lions den, fuck, might as well have a bodyguard." no way he's letting Charlie go back after tonight if it's seedy or weird, they'll just figure something else out.

* * *

It's after dark when the limo comes to pick Charlie and Dean up. To see this kind of treatment, you'd think all exotic work were glamorous instead of horrible, dangerous and terrifying. But, then, not everyone is employed by Celestial.

She's helped into the car by the driver and Dean follows, both in their street clothes (being all they really have) but spiffied up as much as they can manage. Charlie's had her hair cut and tinted in hopes of catching the Billionaires eyes and Dean's cleaned up his stubble a little, which is about as spiffy as he gets.

They barely talk in the car, Charlie excited but still struggling with a small swell of shame brought on by Dean's comments the night before. Dean's taking it all in, drinking from the limo bar and watching the buildings of Manhattan pass them on the way to wherever it was the limo was taking them.

The lack of information about where they were going and who they were working for weirds Dean out but it doesn't take long for the limousine to coast into a circular drive of a tall, glass building that looks more like a fancy upscale hotel than apartments. Driver slows, rolls his window down and has a short, quiet conversation with a man in a grey uniform before circling out of the drive and heading around back to where the limos are parking. They stop, the driver lets them both out and two men with clipboards are waiting for them. They take Charlie's name and her invitation pass and mark Dean down as her plus one, then hurry the both of them in through a service entrance with a few other girls and up an elevator like they're late for something.

Out of the elevator, down a white art deco hall lushly carpeted in rich wine and sconce-lit, to another, more ornate elevator and up one more floor to the penthouse. When the doors open, they're practically already inside the enormous apartment and the party has long since started. The Dolls, as they're being called, are herded in and quickly taken off to a staging area for makeup, wardrobe and a rundown.

Charlie only has time to wave to Dean as he's urged into a room with the only other men, both male model-looking and a little older than Dean. They seem jaded and blase about the whole thing but Dean can't be, not while he's being quickly undressed and re-dressed to fit in with the party. It's not unlike what he was already wearing - jeans, tshirt, boots and a leather jacket - but somehow it looks too fussy on him, too much and he's damn sure it cost more than his dad's car. They try to sculpt his hair but he won't have it and he's out of his chair, swinging out the door without giving them the chance to fix something that's not broken.

When he finds his way back to the party he allows himself to take it in. The penthouse is bigger than he thought it would be, warm cream paint and vanilla lighting, barely any furniture or art. Gigantic windows make up two of the walls and give a stunning view of the skyscrapers around them.

A server walks by with a tray and Dean swipes a beer for himself, a handful of peanuts from a bowl at the bar and he's slowly making his way through the crowd of too-beautiful people. Some of them are new like Dean, they wander around alone trying to make heads or tails of the situation they find themselves in. Some have made the rounds before and they huddle together in packs like popular girls at a high school. They're talking about nothing, pretending to laugh and have a good time but they can't seem to take their eyes off a group of men in nice suits who linger near the fireplace, preoccupied with every pretty thing that walks by them. Dean can't really be bothered, though. He wants to find Charlie, make sure she's alright.


	4. Castiel

Somewhere in the same penthouse, in a room that looks more like a showroom floor than a dressing room, "Is this all _absolutely_ necessary?" Castiel stands on a short step in front of a full length mirror, adjusting his tie while a valet quietly brushes lint off his sleeve. He can see his brothers reflected in the mirror, lounging behind him and looking content as a couple of fat house cats, "I'd like to _enjoy_ my own birthday for once, if that's not too much to ask."

"Cassie, **_baby_**..." Gabriel has to pause in casually checking his manicure to look up at Cas, "Don't you think I _want_ you to have fun? I'm _all about_ you having fun. Parties? Are **_fun_**."

Castiel sighs, waves away the valet and slowly takes a seat for himself on the step he had just been standing on, "You make me sound abnormal."

"Well, you're a _freak_ so there's that." Balthazar chimes in, halfway through a bottle of champagne although god knows where he managed to get it.

"Thank you." grumbles Cas, resting his shoulders back against the mirror behind him. The one thing he would pay a million dollars to avoid and it doesn't look like there's any getting out of it. How cliche it all is.

" _Normal_ people have birthday parties, Cas." As if anyone asked Gabriel for his opinion. He crosses his legs, looking grander in presence than he is in stature, "Find the fun button and **_push_** it."

"Gabriel, you're wearing thin my patience." But there's no menace to it, no venom, and it's weaker than he wants it to be. Castiel slowly stands, brushes at his own shoulders, "I just want _one night_. One night talking to someone real, not surrounded by those vapid Dolls..."

"Real? _Pfft._ " Balthazar's not really in the conversation but he does like to stir the pot, "Real people are **overrated**."

Gabriel chuckles at stands as well, giving Castiel's weirdly twisted tie another fix, "So come for the cake then go home. Or, hey, wander around town and talk to random scum? Move a few rocks, get your groove on. You don't wanna party? Fine. _Your loss_ , Bucko. But you gotta stay for the big surprise, alright?"

Castiel remains quiet through Gabriel's chatter and only sighs in response. At least he won't have to waste the whole night with these people.

* * *

The party is everything Castiel thought it would be. Pretty people he doesn't know, party drugs, a tap that never runs dry and music he can't stand. And everywhere he goes he feels eyes on him. Yes, he doesn't know these people but they sure as hell know him. Architect Castiel Shurley, son of author Charles Shurley. Worth 2.75 billion dollars without the wealth of his father's estate and better known for his aggression - wrestling and kick boxing - than for any stupid building he's ever designed.

He's a catch, Castiel. Rich. Good looking, looks younger than his 38 years, slim built and strong but in the possession of an irritatingly intense personality. He's a dud. His brothers are all fun, playboys who are the life of any party and seem to fit in wherever they go. Casual flings, fake people, they don't bother the other Shurley boys.

Castiel would rather hide than do what he's doing right now. He can't mingle because he has no real personality and can't fake a conversation to save his life. He can't drink, it doesn't really do anything for him except make him a little irate bastard. So he sits at the bar with a cherry 7-up on the rocks in a highball glass, trying to scoop the maraschino cherry out with a spoon for lack of anything better to do and that's when he hears muffled swearing coming from a few seats down.

A kid, maybe 19, is sitting at the end of the bar trying to wipe cake icing off his t-shirt with a napkin and doing little more than smearing it across the fabric. Castiel smirks, gets the bartender's attention and motions to the club soda. Another cliche but at least it works, sometimes. The soda's poured out and he makes his way to the young man, holding the glass out, "I hope you didn't borrow that."

Dean looks up at the glass, first, and dips the napkin into the soda, "Hey, thanks man... yeah, kinda did. Hope there's not a deposit on this crap." He's seen Charlie since they got there, decked out and gorgeous, looking like she owned the world and it took that long for him to finally settle in to the party. Of course settling in, for Dean, means eating and half of what he ate has ended up on his shirt.

Castiel reaches out to take the sugary napkin from Dean before he can do any more damage with it and gets a fresh one, dampens with soda and starts to dab at the icing, himself, "Well, a casualty of war, I guess. I'm sure it can be replaced." Dean took the napkin from Castiel and he didn't argue, just invited himself to the next seat, "Having fun, casualty aside?"

"What, here? Fff, nah. Kinda off the beaten path for me, you know how it is."

"I do." Shurley sighs and rests against the bar, watching the festivities of his own birthday party pass him by, "Not your _scene_ , I take it?"

"Yeah, well. Guess I don't really _have_ a scene but if I did? Hell. Wouldn't be _this_ , no offense or anything."

"No, none taken. I'm not much for this sort of thing, myself. It's part of the life, though." As if his nanny were behind him, jabbing his ribs for being impolite, Castiel excuses himself quietly and holds out his hand, "Where are my manners? Castiel."

"No, hey I get it. Well, not in the sense of actually getting it but I get what you're on about. But, hey, you gotta do what you gotta do, right?" taking Castiel's hand, shaking firmly, "Oh, hey. Dean." It takes Dean a second but the man's name grates on him, he makes a face, " _Castiel_? Don't take this dirty but that's mouthful right there."

He laughs, he can't help it, "You're not wrong. My father has some sort of fetish for unique names I imagine."

* * *

It's a solid hour, maybe more, into Castiel's attendance. He and Dean have moved to the bend in the lone sectional couch, gabbing the night away about whatever pops into their heads. At first it was Dean telling weird stories about his braniac little brother and the good times they'd had before they went their separate ways. Now Castiel, griping through horror stories of his upbringing. Of Au Pairs, a bitchy butler and annoying his father's drivers.

"Wait, wait, hold on..." Dean's laughing harder than he has in a long time, his mouth stuffed with crackers dolloped with some kind of fish salad. Stuffed in his cheeks like a squirrel, "You're telling me you never learned to drive?"

"Well, I wasn't given a second chance after that." Castiel's lounging, looking more casual than he usually does, sipping at another mocktail and laughing along with Dean, "Can you really blame them?"

"Yeah, guess not." he's not thinking when he puts his feet up on the coffee table, ankle over ankle, arms folded behind his head. Takes a few seconds of mulling it over and then Dean pipes up again, "Could teach you? I mean, I don't exactly have a car anymore but I figure, basics?"

Castiel looks puzzled for a moment, over thinking it all, and before he's able to answer their conversation is interrupted by Gabriel and Balthazar, both seeming pleased as hell with themselves. It's Balthazar who speaks, "Sorry to interrupt, _you lovely Party People_. Mind if I steal my brother away? Important party business."

Dean and Castiel both stand at the same time and Dean, surprised, shrugs, "Naw, hey that's cool. Party business."

Castiel shrugs, too, trying to tell Dean that he's not sure what's going on either as Balthazar wraps an arm around his shoulders and starts to walk him away. Gabriel watches them go and then discreetly takes Dean aside, walking him towards a hallway, "He won't be long, hour or so tops. But I'm more interested in you."

"Me?"

"For a private, uh... _show_. See, this is a _birthday_ party." Gabe motions to get the attention of an assistant and three come slithering out of the crowd to follow the pair, staying behind as they walk, "And we think you caught our birthday boy's eye. We want him _happy_ , right?"

"R... ight." And Dean still doesn't follow, preoccupied with the overly swanky group behind them, "What's that got to do with me?"

"Well, birthdays mean presents." A good looking man in a pink polo shirt catches up with Gabriel just long enough to hand him a clip board, which he starts looking over and making notes on, "You, my friend, are the present. Get me?"


	5. The Show

Yeah, it's really taken Dean this long to remember what he's there for, what he is. He's a doll like the rest of them but that doesn't mean he has to go through with this, right? He clears his throat, tries to get Gabriel's attention, "Uh, look, there... whatever your name is. Hey, I'm here for the booze, nuthin' else. One of the others filled me in, said I don't have to do the private show thing if I don't want to and, oh man, I do not want to."

Gabriel finishes his chore and snaps his fingers at the group behind him, " _Deshawn_? Where's Deshawn?" The man who'd given Gabe the clipboard jogs up to take it back. Dean gets Gabriel's attention, a little smirk, "Well, you don't have to, no. But we pay real good and for a first timer on a special occasion who looks the way you look? Wow, four figures, my friend. On top of whatever birthday boy shells out for your, ahem, shall we say 'services'?"

Dean pauses and, within a few steps, Gabriel's stopped short, too. He can see Dean wrestling with the choice and sighs, taking the clipboard back from Deshawn and flipping the papers over until he gets to the agreement form. It's shoved into Dean's hand, along with the pen but only after Gabriel circles the more than six-thousand dollar bonus for this job and strikes next to the standard bonuses: Up-close examination for four hundred, simulated masturbation for one hundred, real masturbation for three. Client privileges to touch the entertainer are eight hundred and there's an ominously unlabeled check-box with fee caption of, 'double fee'.

"Sign here, here, initial and read the fine print. If you check any of these boxes you're entitled to the pretty little bonus next to it. All good? **_Goooood_**."

"You know I'm not gay, right?" Dean mumbles, reading the contract.

Gabriel rolls his eyes, resists the urge to gag himself with his own finger, "And that matters... why? You're not marrying him, you're the entertainment. Say it with me! _Ent. Ter. Tain. Ment_."

"Right, right." Dean's still reading, he's ignoring Gabe because he has to ignore him to stay sane at this point. It's not until Gabriel physically pushes the pen to the paper that Dean sighs and starts to sign. He stops, though, glancing back at the party down the hall, "How long's this gonna take, anyway?"

"Worried about my baby bro? Don't be, you'll see him again, that's a guarantee. Now, we need your John Hancock _riiiiight there_."

He takes another moment before signing the agreement, signing again and initialing. Dean looks through the bonuses and there's no way he's agreeing to one that's not labelled, he could be signing himself into indentured servitude on a Carnival Cruise ship for all he knows. In fact, most of them look off. Up-close examination's out and he doesn't even know what that means and touching's definitely a no go. But masturbation... it's not like he's not a pro there. Sure, he could go for simulated, but it's a third the bonus and he can't see how it's really any different so masturbation wins and, wow, that sounds weird when you put the words together like that.

"John Hancock..." he grunts, shoving the pen and clipboard back at Gabriel, "Suddenly wondering what the story behind that name is, am I right?"

If Gabriel thinks that's funny, he's keeping it to himself, "Alright, you're ready for wardrobe - fancy term for wearing a robe. Deshawn? Where the heck is..." But Deshawn's already leading Dean away, pencil behind his ear, and Gabe shouts to them, "Take good care of my boy, Deshawn!"

When Gabe's out of earshot, Deshawn finally talks, "It's _Nayshawn_. Prick's been saying it wrong for **three fucking years**." Dean cracks a grin at that and Nayshawn gives one back to him, "Look, don't freak out here. Just relax, it's all good. All you do is take all your clothes off, that's it. Unless you said you was gonna do something else they just stare at that fine ass, get themself off and you get paid. Easy peasy." they make it to a small room at the end of the hall and Nayshawn knocks, just in case, then pushes the door open, "You leave your clothes in there, socks, everything. Put on one of them robes. That top drawer has condoms, lube, whatever if you think you need it. You got five minutes, get yourself out here and I'll get you to Mr. Big."

"Yeah, thanks man." And Dean's in the room, door locked behind him like anybody cares. He has to still his own breathing, didn't think he'd have anxiety about this. He's not even totally sure what he's given his consent to but, hell, it's not life or death. He can do this and, man, he better do it because that's a sweet pile of cash for just showing some horny old guy your ass for a half hour.

A few minutes later he's in the hallway, feeling as awkward as he looks in a very thin blue satin robe that seems designed to show everything off. Nayshawn's talking to a girl with blonde and pink hair, and Dean clears his throat to get his attention, "You got everything you need? Y'ain't coming back before it's over so you damn well better."

"I'm good. I'm... I'm good."

"Well, come on then." Nayshawn's got Dean's arm before he can argue and they're practically power-walking back down the hallway then right into another hall. They stop outside a room, door open and practically pitch black save a spotlight shining on a nicely made bed. Nayshawn takes Dean aside, "Listen, you're the one in control, here. You call the shots, don't let anything happen that you didn't agree to. They get mad? Pssh, please. Who gives a shit? They still got to pay you. Stand up straight, you'll be alright."

"Thanks." Dean seems to release a breath he's been holding in, "Thanks a lot, dude."

"Yep. Okay," He reads through a few pages of the clipboard, "It says here you're gonna do the full on self love, hey now! See, that's brave. Now you get in there, do your damn job. You need me and I'm around." He's already halfway down the hall when he mouths to Dean, "Be around this way in forty-five."

Courage was easy about thirty seconds ago but now that he's alone Dean can feel a sinking. He pushes through the door and closes it behind him and slowly makes his way to the bed. He tries to sigh, or breathe, facing the bed just to be in the light.

Suddenly he hears a man's voice, deep and quiet, almost a catch in his throat, "Disrobe... _slowly_."


	6. Disrobed

**Notes for the Chapter:**

> Finally to the smutty stuff!

Balthazar has a firm hold on Castiel's shoulders and they leave the party via a hallway on the other side of the room. He tries to look back as his brother whisks him away, trying to catch a glimpse of Dean. Castiel has finally met someone he can have a real conversation with, who's a person, who doesn't seem to care about his money or estate. Who hasn't made a move on him all night. Of course, trust his brothers to get in the way of the good time he was finally having.

They turn into another hall and Balthazar starts to move Castiel toward a room he knows to be a 'bedroom' in this horrible show penthouse and he stops, forces Balthazar to stop, too, "No." He sighs and starts back, "No, you celebrate your way and I won't interfere, please let me celebrate mine."

But Balthazar has him stopped and turned around just as quick, locking arms with his brother, "It's your birthday, we went to _all the trouble_..." and before Castiel can do anything about it, they're both in the dark room through the client's door at the back. Hidden by the darkness outside of the spotlight, whispering, "Don't you want to get back to your young man, Castiel?" Balthazar starts to walk Castiel forward but stops halfway through the room, "Be able to talk to him, have a good time without worrying? He doesn't know you want him yet but everyone else does. You _pitch a teepee_ at a birthday party and you'll scare the poor bastard off."

And it's not until Balthazar motions to the man in the spotlight, built like a god with his back to the audience, that Castiel even realizes his entertainment is already there. He wants to say something, to protest but he can't find words.

Balthazar speaks up, "Disrobe, _slowly_..." and at that there's a hesitation on the part of the Doll, just a moment, enough to tell Castiel that he's not the only one in the room who had never done this before. Slowly, the Doll opens the robe and shrugs it off of broad, muscular shoulders. He lets it slide down his arms, his tan and freckled back and finally pool it at his feet revealing a tight, sculpted ass. Castiel is mesmerized by his body, so much so that he almost jumps when Balthazar pats his back and whispers, "He's checked the 'masturbation' box, you lucky devil. Talk dirty to him, they like that. Don't flub this, baby brother. Get your jollies out and come back to the party."

To the Doll, Balthazar continues, "Face down on the bed, **ass up**." He winks at his brother and takes his leave, back into the room somewhere to quietly slip through the client doors and leave Castiel alone with this... masterpiece. And he frankly doesn't know what to do. It takes awhile but he moves forward, to the seat meant for the client just outside the circle of the spotlight. He's almost close enough to touch but, although Castiel has never done this before, he certainly knows the rules.

A deep breath for courage and Dean does what he's told, yet again. He bends his body forward, resting his chest against the bed, cheek on folded arms, feeling incredibly exposed.

And it's awful to admit it but Balthazar is right about Dean, about how Castiel wants him and doesn't want to blow it so soon. His brother is also right on another count. He can't go back to the party now, not after seeing this hot, athletic body on display for him. He wouldn't be able to talk to his new friend without imagining this body with Dean's face. Dean's gorgeous face, his mop of hair, green eyes... amazing smile... Dean who was young enough to be Castiel's son. It's been so long since he's connected with anyone like this, had fun like this, does he really want to spoil it by spending the rest of the night unbearably horny?

Reluctantly, Castiel takes the seat provided for him - 'talk dirty to him, they like that' - and clears his throat, trying to remember the advice he's been given, "Spread..." the gravel of his voice feels rougher now, his mouth is too dry. He really should've asked for another 7-up. Castiel takes a deep breath and speaks up, trying again, " _Spread your cheeks_... show me your ass hole."

Dean's been wondering what was taking so long until, finally, he's been given some orders. He bites his lip and unfolds his arms from beneath his head, reaching for a pillow to replace them so that he doesn't have to push his face into the mattress. He stills a moment and then does what's asked of him, reaching back with both hands to grip his ass cheeks and gently pull them apart. He hears a soft grunt coming from his client and, from the position of his face pressed gently into the pillow, he can kind of look down his own body and, between his legs, can barely see the man sitting behind him, shadowed from the waist up and with a definite bulge in his pants.

And Dean should hate this. Hell, he thought he would, he thought it would be stupid and he would feel cheap but the thing is... he kind of does feel cheap. And vulnerable and on display, like he's being used and he can't believe how much it doesn't suck. The feeling of being at someone else's mercy, being a toy for their pleasure. Feeling like, even though he knows it won't happen, that man can always stand up, close the gap between them and have his way with Dean. Hates to admit it but that thought, and the realization that his body is visibly turning this man on, is making him harder than he's been in recent memory.

Yeah, Dean's not into guys - if anybody asks. But even Charlie knows that's a straight up lie.

It must be visible already, too, because he can see the man reacting to him. Palming his own cock through his pants, taking in a breath. After a long minute or two of this exposure, of Dean displaying himself for this stranger, the man speaks again, and it's still nervous but the way he's talking is getting more forceful, "You're going to put on a show for me... stay in that position, stroke your cock. I want to watch you pleasure yourself."

This is the harder part. Dean's not new to getting himself off, not by a long shot, but he's never gotten himself off for an audience before. But his time is limited, here, and he finds himself wanting to make the stranger horny, watch him rub himself, make him come at the sight of Dean in a sex act. Dean wants him to get his money's worth, after all they're paying him a lot for this and for the moment he neglects his cock to reach back again and gently rub the pads of his fingers against his hole. God, that feels good, tender and the feeling goes straight to his cock. He tries to focus on the job but all he can think about is the stranger's mouth on his shoulder, cock in his ass and the fantasy of it makes Dean moan.

He doesn't know when he spit in his hand, started stroking himself, fondling his balls, the other hand still busy rimming and rubbing his hole but when he's once again aware of reality he can see that the stranger has taken his own cock out, softly jerking and getting himself off to Dean's body. His dick is big, hard and Dean's thinking, again, of how it would feel in his ass, in his mouth. It's not something he's ever done out of fear of what people would think, what his family would think, but being this close to it makes one thing perfectly clear - it's what Dean wants.


	7. Brutal

**Notes for the Chapter:**

> Short chapter to tide you over while I work on another fic, bit smutty, hope you like it!

The display is magnificent. It's intense, sexy and driving Castiel out of his mind. Not because he's turned on, though he's clearly that, and not because he's upset over objectifying another human being. In fact, the power he has over this beautiful creature is greatly responsible for the stiff, aching erection in his hand. No, what's really weighing on Castiel's mind isn't the morality of the situation, it's the fact that if he had his way he would be fucking that Doll raw right now. Hard, numbing and jarring, fistful of his dirty blonde hair.  
  
He's going through the motions in his mind and he's close enough to start, all he has to do is reach out and run his fingertips between the Doll's cheeks, start to gently finger him open even though 'gently' is not in Castiel's nature. He might cup his balls, suck them, but foreplay is boring. What he wants is the fuck. To hear the Doll's breath hitch every time Castiel's hips roughly meet his haunches, cry out in pleasure when Castiel's hand jerks him over the edge. To use him, leave him lying face down on this bed in an all-over heat blush, gaping and leaking. But if he's good at anything it's self control, touching himself will have to do for now.  
  
Sure, the gossip hounds know who Castiel is, what he's worth, where he vacations. But the man, himself, is a bit of a mystery. They likely can't tell you that Castiel is not a tender person, not by any stretch of the imagination. To get along in polite society he affects quiet, gentle. Mild mannered. But put boxing gloves on him and he's nothing short of a brute. He can't think back to a time when he's made love, been soft or sweet. Or been in love for that matter, now that he's thinking about it.  
  
His last relationship was with a pretty gold digger named Meg. She was his brother Lucifer's favorite Doll before she made her way to Castiel, when he found her in his bed clad only in his bed sheet and a grin during one of these ridiculous soirees. Smooth white skin, firm breasts, dark hair and wicked eyes. Meg in his bed was therapeutic to say the least, the only woman in fresh memory to really get him. Really, the only of his recent conquests to appreciate a hard, brutal fuck.  
  
Still, a gold digger she is and Lucifer made her a better offer. Castiel can't say he wasn't sad to see her go and he does get a pang of regret when he catches sight of her now and then. When she smiles at him from across a room. But what's done is done and that's not love, though she played her part beautifully. Still, a Doll isn't a person, per se. The person is the one who collects your money after the performance, be it a witty conversation at a party or a lewd act in the back of a limo. They're paid to do what they do. To be perfect, to be sexy and good in bed, to be interesting and interested in you. Once they go home, the Doll disappears. They aren't real, don't exist and you can't love something that doesn't exist.  
  
You can miss it, though.  
  
It's been long ago, now, and Castiel's brothers are right as much as he hates to admit it. He needs to replace her. He needs to get laid, badly. And he's desperately trying not to think of Dean, not to imagine him as this Adonis but he can't. It's too late, Dean's in his head and now he's watching this man rub one out and finding that not seeing his face allows the fantasy to continue.  
  
Suddenly the Doll moans, it's aching and loud. He's still fisting his cock but it's slower now, he's taking his time, working himself through an orgasm that tightens his thighs and cheeks and begins to spill him on the ground and the bed sheet. He rolls a cupped palm over his head and it's got him moaning again, smearing come in his hand and back down to his balls and the sight of it's got Castiel choking back a moan of his own. He feels his own balls tighten, he's coming, and he reaches for one of the wet wipes he was given to keep from making a mess of his suit.  
  
Castiel doesn't say anything after. More wet wipes, he cleans himself thoroughly, ignoring the spent Doll who has no idea if he's allowed to move. He gives the Doll one more look over before he excuses himself, heads through the darkness to the back of the room and slips out quietly.  
  
Once he's out of the room, in the hallway he's confronted by his smirking brother Gabriel which is basically the last sight he wants when he's still so sexually worked up. He's trying to breath it out, slow his racing heart when Gabe starts to drag him back to the party, "See? Now, that wasn't **_so_** bad, was it?"  
  
"That Doll... is he _new_?"  
  
Gabriel only shrugs, " ** _Maybe_**. You _likey_? His name's D-" but Castiel holds a hand up to cut his brother off.  
  
He shakes his head, sighing, "I don't _want to know_ his name, Gabriel. I _want_..." Castiel takes another breath in and sighs it out, slowly, "I want to set up another performance... and. Double his pay for this one if he agrees to not take on other clients."  
  
To say Gabriel looks shocked is an understatement, "Well, well, well... looks like I sure can pick em, huh? You got it Cassie, he's **_all_** yours."


	8. Anna

**Notes for the Chapter:**

> NOTE: A little bit about what happens with Charlie while Dean's off with Mr. Big. ;)

If you had asked Charlie earlier this month if she could see herself in a fancy designer dress, rubbing elbows with celebrities and the gorgeous, loaded Shurley family you would have gotten a resounding, 'No!' - and yet here she is, decked out in a beautiful green number. Short, tight and sheer in all the right places. Her tiny feet seem two sizes larger in clunky wedged booties that just wear ugly in her eyes but the point is to make her fit in and everyone else seems like the entire room is awash with pretty girls in tiny dresses and big, clunky booties.

She's been having fun, as much fun as a girl can have when they know what awaits them at the end of the night if they catch someone's eye. But that's what she wants, this could be exactly what she needs to stay independent and, really, that's all she's ever wanted for herself. That doesn't seem to make it any less scary.

But she's been here once before and somehow it seems to make her old news. Caught someone right out of the gate last night but tonight is a different story. Tonight she's being ignored. So Charlie is doing what all the girls are doing right now. She's drinking, making herself look available and eyeing the stoic and confidant group of handsome men who gravitate towards each other and check out tonight's variety.

The Shurley boys. Flanked by the few Shurley sisters and some of the favored, exclusive Dolls. All in nice suits, all with drinks in their hands. None of them really Charlie's... type. Not that it matters.

"See someone you know?" A girl about Charlie's age swipes her empty champagne flute and replaces it with a full glass from a passing tray, "You look like you're concentrating."

She's gorgeous. Suit-clad and classy. A sweep of artfully styled cranberry red hair French rolled and pinned to the back of her head, matching lipstick and great big eyes. Charlie doesn't exactly know what to say and she's trying so hard not to blurt out how much she looks like an anime character.

"Uh, yes. No... um." Charlie tries to smile and manages to look nervous for her trouble, "Hi. Charlie. Me. I'm Charlie."

The girl sets her own drink on the fireplace mantle and takes a step down away from the hearth, "I know who you are." She settles on the step next to Charlie and smiles, "I'm Anna. Shurley."

"Anna Shurley..." As if Charlie can't help herself, "Like Anne of Green-" and before she can finish, Anna rolls her eyes and raises a hand to stop her.

"Yes, like Anne of Green Gables." Anna sighs, repositions, tucks a leg beneath her and rests her brow against her palm. For a moment she looks irritated and Charlie is silently berating herself for being so cheesy when Anna cracks a small, sexy grin from behind her hand, "God, I'm so over that joke." she's still grinning at Charlie when she folds her arms across her middle, "My eighth grade teacher made us read that and I never had a day of peace and quiet again. Not in school, at least."

The ease with which Anna presents herself is a blessing, it puts Charlie at ease, too and lightens her up. She does, however, manage an awkward, "Right, sorry." while thinking for just the right thing to say. It's a long silence before she comes up with, "Um. How about that... local... _sports_ team?"

"I'm not big on sports."

Charlie let out a breath and cast a glance up to the ceiling, "Thank _god_. I mean, heck I know my way around a Fantasy Football game but put me in the bleachers and I'm L.O.S.T., _lost._ " and, after a beat, she glances over at Anna then downs a courageously large amount of her champagne for the courage to continue, "So, you're a Shurley? I mean, and don't get ticked at me for asking, but why aren't you over there with the other Kardashians?"

The way Charlie is bastardizing the English language seems to tickle Anna and she shakes her head, chuckling, "They're boring, every party is the same. The same people, the same food." she motions to her group of brothers, all scoping out a newer Doll and it's not subtle, "Same grody conversation. Besides. You're... cute. I _thought_..." her hand finds Charlie's knee gently, smoothing softly and slowly up her inner thigh to the hem of her dress, "Maybe we could do some business? Only if you _want_ to. I mean... I've never done this before."

Anna's hand brushing the length of Charlie's thigh is new, kind of unexpected and makes her bite gently at the inside of her cheek, take in a breath. She doesn't even know if Anna is legally allowed to do this but those eyes, those lips... she can't say she minds. She can't say she doesn't want to take Anna home and spend the night slowly turning her inside out. It's not love at first sight, that's a fairytale. But there's definitely lust. The way Anna moves, the way she crosses her legs. The hungry way she looks at Charlie, pink tongue gently brushing against her top lip like she can't help imagining what Charlie has under her clothes. And even if it's all going fast she has to remember that it's meant to, that's the way the cookie crumbles in this business. Ideally, she would chat up a sexy girl at a bar somewhere and they'd enjoy each other that night if things went well, but this isn't an ideal situation and Charlie has to be realistic about what's being suggested, here.

Anna wants her to sign a contract that gives her control over Charlie's body, to objectify it, maybe touch it if the price is right. To watch Charlie perform in the most intimate way she can think of and it's to be entirely one-sided. But that's what tonight is about and even if it's not ideal, it's the promise of a paycheck, "Well, that's what I'm here for... right?" Besides, Anna's drop dead gorgeous and a woman, and that's a lucky draw combination that she might not get again.

* * *

It's not even a half an hour later and Charlie is being whisked down the hall in her flimsy robe, lead to her destination by another Doll wrangler, a pretty little blonde thing named Penny. She has the clipboard Charlie will have to look over and sign and they stop right outside the open Bedroom doors to finish business, "Sign here, initial here and here and check your boxes. Do you need anything? Toys, lube?"

"This box," Charlie speaks up, tapping the un-captioned checkbox with the button-end of the ballpoint pen in her hand, "What happens if I check this box? I mean, why doesn't it have a description? It's not a _snuff film_ thing, is it?"

Penny's tired, it's been a long day and she shoves the clipboard at Charlie, "Sign here, initial here and here and check your boxes. But if you want my advice? Don't check that box, those Shurley's can get pretty _demented_ and you've got that whole innocent schoolgirl thing going on. They'd be all over that."

"So, _snuff film_." Charlie states flatly. It's supposed to be a joke and it half is but she rolls her eyes and tries again, "Seriously, tell me. What's this box for?" She can tell Penny won't budge until she starts signing her body away so she goes about it, glancing up at her wrangler now and then, "Can't you just gimme a hint or something?"

Once Charlie is cooperating, Penny sighs, leans against the wall and reaches out to tap the unmarked checkbox with her fingertips, "That's the box you check when you want the full option. Like, if your host wants sex and you're cool with it, this is the box you check. Unless you check this box the most they can do is touch you. No penetration, no mouths, no rubbing of genitals, nada. Not even _kissing_ , it's kind of depressing. Especially if you get on with them really well."

And, no, Charlie is not prepared for that. She returns Penny's sigh and checks the boxes she's comfortable with, "Yeah, but what's stopping you from just chatting them up later? Who needs a contract when you've got cheesy pick-up lines, right?"

The clipboard is handed back to Penny, who looks it over to finalize the selections, "Masturbation, examination, touching. Wow, everything but the kitchen sink." She glances up at Charlie, seemingly a bit weirded out by her questions, "Uhm, _no_? Dolls don't date the Shurley crowd. Actually, I don't think they date at all. I'm starting to wonder if this is how they get out their ya-ya's or something."

"Oh... right." Charlie flinches, she can't help it. Oh well, a paycheck is a paycheck.


	9. Kept

**Notes for the Chapter:**

> Heads up, for those it might trigger, Dean goes on an internal monologue rant here about why he likes prostitutes - it's supposed to be played for laughs but I can totally get how it might upset some people, so I wanted to let you know in advance! :)

The room is silent except for the scrape of shoes, door hardware twisting, opening in the distance somewhere behind him. And Dean doesn't feel like moving, doesn't even know if he's allowed. He wasn't left with instructions and he doesn't know how all this works yet.

So he stays, stock still and waiting and finally after what seems like forever he feels the cool satin of a fresh robe around his shoulders, a friendly hand at his back. Nayshawn, kind smile and pencil behind his ear, "Damn, I don't know what you did but you did it good."

The voice, already familiar and comforting, feels like the permission Dean needs to finally breathe. He pushes up from the bed with his hands but it takes him a full minute to stand under his own power, "Hah?" It's not that he's not listening to Nayshawn, he is. He's also looking over his shoulder at the gentle light that outlines his client's escape door, far at the back of the black room. It's hard to see, still standing in the spotlight, and he's barely aware of his new friend closing and tying his robe. Checking him over to make sure he's okay.

" _Hah_? What do you mean, ' _hah_ '? You better **_wake the hell up_** , Winchester, or you're gonna miss a pretty sweet payday." It's then that Nayshawn shoves the clipboard he's been holding into Dean's hands along with a pen, "That's all the agreed on and twenty percent. Double if you agree not to take any other clients because Mr. Big's got his eye on you, _whoo_. And he _never_ pays for Dolls. Doesn't have to, not the way _he_ looks. Rumor has it he hates Dolls, anyway, so you worked yourself a Gee-Dee miracle. You just sign right here, and here if you wanna be kept."

 _Kept._ Dean only hears about half of what Nayshawn is saying but he's sneering as though he's been hanging on every word. He signs for his money then tips the clipboard back to his friend, "Yeah, no. I'll pass." The door seems farther than it is in bare feet on a cold floor, trying to walk after what just happened but he's determined to be a man about this. Dean Winchester is nobody's pet. Nayshawn only rolls his eyes and follows, checking over the contracts.

This isn't right. Dean should feel dirty or ashamed of what he's done but mostly he just feels regret that his first experience with a man was borderline prostitution. Not that he has anything against prostitution. Hell, if anything, prostitution is mighty neighborly and it's hard for Dean to find it in him to look down on a profession he's been on the John side of for the last few years. Boobs, bouncing, orgasms and sometimes latex - all for a fair price. What's not to like? Okay, yeah, he might be on the wrong side of this argument.

Anyway, at least it's over and done with. He's gonna get a fat check, he got his rocks off with a guy who's dick should be in the Guinness Book and he never has to think about him again, ever.

Eh, maybe not ever. Actually, ever's a pretty damn strong word...

Dean's silent on their way back to the dressing room while Nayshawn talks his ear off about what a mistake he's making but Dean doesn't really hear him. He's playing over the events in his mind, the dark room and cool air. Being on display, at someone else's mercy. Watching the stranger stroke his dick at the sight of Dean's naked body, his sex act, rubbing his own cock and the wash of desire to be fucked and used by a man he's never even seen. Hard enough to admit how much he wanted it to himself, add to that the man's desire to keep Dean on a leash like that and it's just all too much to deal with. Especially knowing he could always check the unlabelled box with the hope of being fucked into that mattress by that beautiful cock for a half hour and no one who knew Dean would ever have to know.

He doesn't remember Nayshawn leaving him in the dressing room, he barely remembers locking the door and fumbling through their dressing table for lube. Dean has been too in his own mind and now he's shed his robe and is leaning against the door frame, slowly jerking his cock at the thought of letting this Mr. Big have his way with him. He rests his head on the arm braced across the frame, muffles a moan into his hand while his other lube-slicked hand fondles his balls, cups, then makes it's way up to his head. Images in his head of the man - cock rock-hard, pulled through his fly - in the shadows standing up, walking towards Dean while slowly stripping his suit coat off and loosening his tie. Buttons open down the front of a crisp, white shirt and it's down his strong shoulders, down his arms and onto the floor. Dean can almost hear the jingle of his belt and fly as he unfastens his pants around his aching dick. Takes Dean's hips roughly, pulls him back against that cock and rubs a hot, rigid shaft between Dean's cheeks. And he's so close, Dean rubbing and jerking, hips rocking forward as he fucks his fist. He can feel the tightening in his ass, his balls, he's about to spill over the edge when there's a sharp, loud knock on the other side of the door that has him stumble a few feet away.

Gabriel's voice sing-song's from the hallway, " _All done in there_ , Champ?"

Fuck, Dean can't believe how much he wants this but he'll be damned if he's _owned_.


	10. Afterward

**Summary for the Chapter:**

> Dean and Charlie tumble out of a good night.

**Notes for the Chapter:**

> This is a VERY short chapter just to let you know I'm still here and haven't abandon this story! The truth is that I just work all the time and it makes it hard to find time for my fanworks. It might take me a little bit to get back into writing, though. Thank you for being patient with me! And for your comments and support, you have no idea how far a little encouragement goes. :)

When all’s said and done, and Dean comes out of his funk long enough to notice his surroundings, he finds himself sitting on the brick in front of the fireplace with a red, velveteen envelope clutched in both hands. He’s cleaned himself up, put his own damn clothes back on and, like the good pseudo-brother he is he’s waiting on Charlie. Even though he’s beyond raring to get the actual hell out of this place, away from these rich-ass John’s and their glorified hookers. The ranks of which he finds himself counted among and it leaves a crappy taste in his mouth.

Still doesn’t exactly hate it, that’s the worst part. No, that’s bullshit. The worst part is that the damn ass-out session he was hijacked for cut into the good time he was having at the party and, even though he’s been dry and dressed for almost an hour, he hasn’t seen hide nor hair of Castiel. Probably just as well.

It’s got to be midnight, by now. One in the morning, maybe, and the jolly crowd hasn’t thinned much. For a supposedly wild party, where the champagne is obviously flowing, no one seems all that drunk. Like they’re all trying to look tipsy for affect, as if it makes them more attractive, but the truth is the Dolls are trying to keep their wits about them and Dean can understand why. He doesn’t wanna know what he’d have signed if he’d been drunk. There’s probably something in the fine print about that.

Feels like it’s taken forever, when Charlie emerges from a door on the far side of the room from Dean, smiling in that knowing, sexy way women smile when they’ve just had a good night. She’s not alone, though. Close-talking a pretty red-head in an expensive suit, sporting that same smile. They’re both a little flush, a little sex-drunk. Her hands gently find Charlie’s hips and, whatever Charlie’s whispering to the woman has her closing her eyes, biting the corner of her mouth.

Okay, so Dean’s having a hard time looking away. And maybe having a hard time not imagining what must’ve happened between the two of them. Sue him.

The two women come very close to kissing. Foreheads touch, bodies relaxed against each other’s, when the woman in the suit breaks away and disappears behind the door they’ve just come through. Charlie takes a breath so deep it’s visible from across the room, closes her eyes and leans back on that door. Uh-oh. Dean knows that look. It only takes her a moment to compose herself but, when she spots Dean and starts making her way through the crowd, she’s grinning like an idiot.

A _happy_ idiot, though. Whatever Dean’s problem with this place, it’s nice to see Charlie smile.

Dean starts to get up but Charlie’s already plunked herself down beside him, crossing her legs, leaning back against the wall next to the fireplace. She doesn’t even ask Dean how he is, or if he had a good time. Just beams and asks, “Did I **_tell_** you, or what?”


	11. Zombie

**Summary for the Chapter:**

> Dean's not thinking about Cas.

**Notes for the Chapter:**

> Another short-ish chapter, actually meant to be part of the last one (oops). Sorry, guys! The shorter word count makes finishing more manageable with my schedule. Thanks for understanding!

Dean doesn’t remember coming home, doesn’t remember the shower although, clearly, there was one. He barely remembers putting his socks on the next morning and catching the train to go out and find his next job.

That’s what happened. Job after job. Digging a ditch. Hauling wood. More landscaping. Day in, day out. He doesn’t need the money, either. Not after the night of the party because the check cleared and that one engagement made Dean more money than months doing temp work but whatever happened that night went and messed him up, just enough to make the daily grind of temporary shifts and manual labor seem like a good way to take his mind off things.

When his alarm goes off, instead of punching ‘snooze’ and getting five more minutes, Dean’s up with the buzz but he’s lackluster. Zoned out. Through his shower, though his Cheerios and even the zombie-walk he has to take through the brisk February air to get to the train. He doesn’t live in his life, anymore. Doesn’t think about it because when he starts to pick his head up and look around, he starts to feel played and disgusting. And pissed.

Pissed at himself as much as the situation he was put in. He walked into it, eyes wide open, knowing what he was signing and that’s all well and fine but he still feels like punching a wall until something starts to bleed.

Not too fond of the way Castiel keeps popping into his head, either. He’s a chump, having one conversation with a straight-laced guy at a party and letting it fuck with his head like this. The second he walked out of that cattle call, Cas forgot all about him and found someone else to entertain him. He’s not thinking about Dean so why the hell should Dean be thinking about him? Right? Right.

He is, though. He’s trying not to but he can’t stop. The innocent way Cas laughs when you tell him a joke that’s not even that funny, the way he growls his political opinions like he might turn into a hell beast and tear you limb from limb for opposing his views. How his emotions roll like heavy clouds through those stormy eyes and give him away when he’s trying to be coy. Ah, screw it. Dean only talked to him for, damn. He doesn’t even know how long they talked but it wasn’t long and he’s the only one who gives a crap.

Somehow, Charlie’s doing great. They’ve barely spoken in the two weeks since the party but he sees her, sometimes. In the hallway, blinged-out all to hell and back. Sometimes alone, sometimes with Anna who now knows Dean well enough to shoot him a friendly, ‘Hey, Dean.’ when they cross paths.

Clearly, the bastards can make house calls. Not that Dean cares because he doesn’t. So, no. No craps given. Dean’s moving on with his life starting right now, call it his super-friggin’-late new year’s resolution. No craps, no more.

His pity party’s cut short when a little, grey hand reaches out to pat him on the shoulder and Dean turns to see the kind, pitying smile of a tiny, elderly Native woman who can’t help but get involved with his life, “You poor kid,” she says, “It’ll get better. You’ll forget her, whoever she is, and it’ll get better.”

“Yeah,” Dean’s smile is tight and irritated when he responds. He reaches up and drags his beanie down over half his face for comic effect and mumbles, “ _Thanks_ for that."


	12. Party of One

**Summary for the Chapter:**

> Castiel's been seeing Dean every night and it's doing more harm than good.

**Notes for the Chapter:**

> This is a relatively smutty chapter! I'm in the process of writing a non-Disrobed-related drabble based on the newest season of SPN ( I've decided to fix a scene. ;) ), so I might post that next and add another chapter, here, after that. Sorry for the possible wait!

Dean's got a great ass. The muscle and freckling on his back and shoulders seem there, specifically, to lead your eyes downward. It's firm, tight. Sculpted by hard work, not a gym membership. He's tanned, toned. A thing of beauty. Round enough to bounce, deliciously, when it meets Castiel's hips in a thrust. To feel so good beneath his hands.

This is the third time in as many days that Cas has had Dean in the spotlight, cool and dark 'bedroom' around them. That he's left the audience, bent his prize over that bed and trapped him between an aching cock and a firm mattress. Usually, Dean's good to let his face be mashed into the satin pillow cases. Seems to enjoy it, actually. Long, slender fingers owning a fistful of his hair, what little there is of it, to keep him that way but it's different, tonight.

Dean broke the routine. Felt one of Castiel's hands on his hip, the other taking the scruff of his neck, ready to pin him down but it wasn't enough. He's sex-flushed, already. Breathing deep, eyes dark and dangerous when he turns to catch Castiel's gaze over his shoulder, reaching back to grab his wrist. He's gonna be kissed, god damn it. Being used is awesome, gotta love being used, but something in him needed that connection. To see if there's a spark that can't be explained away by teenage hormones in the presence of a sexy and powerful man.

He didn't have to ask for it. One look, intense and horny as all fuck, and Cas let Dean's hip go in favor of taking a handful of his jaw and practically hauling Dean over his own shoulder for that first kiss. Intense, so deep and rough and needy. Harder than it should be, at this angle. Castiel draping Dean in his arms, folding around and pulling that gorgeous, freckled body back against his own chest. Dean knows how to kiss, too, and that involves teeth. And, just like that, Cas breaks the thing and takes both of Dean's shoulders in his hands, turns him so they're facing each other.

Dean's taller, he's only now really aware of it, having to look up into his eyes. It doesn't matter who's physically larger, though, because it's Castiel who's intensity is radiant. Bit like a halo, surrounding him and charging the air with the electric crackle of a dominant man. His hands ease heat across Dean's chest, down his sides. Cas advances and Dean, as if bewitched by it, backs onto the edge of the bed. He's backed, further, slowly lying back as Cas comes closer. Finishing off the buttons of his white shirt, enough to open it but not remove it. Then his belt, his fly. He's starting to love this, the way Dean likes it when Cas fucks him half-dressed. He likes it, too. There's naughty feeling of control, there, for Castiel. Half in his suit, enjoying a man who's already naked, on display for him, but he's not sure what Dean gets out of it.

Dean's watching him, almost defiantly but that's the nature of Dean. Castiel's not used to the position, with his man on his back like that, but life is full of these little surprises. Cas moves his hand down Dean's stomach, between his legs but he doesn't touch his cock. Just smooths his palm against the flesh of a tight thigh, his other hand busy kindly, gently easing the anal plug out of his ass. It's dropped, somewhere - the handlers have to clean up all sorts of disgusting things and it's best not to think about it.

Dean moans and it's fucking beautiful, his eyes snapping shut, lids flickering, "Ugh, god Cas..." He's always been sensitive and Castiel loves it when he gets loud, so that works in both their favor. When Castiel starts to slick his hands with lube, gently (and, then, not so gently) rim and stretch Dean's hole he gets treated to those moans and grunts. To Dean sighing his name, begging to be fucked, and Cas is only too happy to give him what he wants but then that damn buzzing starts.

And buzzing. And beeping.

Castiel's eyes pop open, his heart's going a mile a minute but you wouldn't know it to look at him. Being jerked (pardon the expression) out of a nice fantasy by the damn phone going crazy on his office desk. He can't look at it, can't make the mistake of picking it up and seeing the name of one of his brothers while he's in the middle of taking his frustrations out on his cock. So, he ignores it, rolls his eyes at the situation. He tries to put it out of his mind, get back to his man in the life he wishes he had but but he can't. His cock's still hard, hand still pulling and jerking but it's like a bad trip after a good joint - there's no getting it back.

Gabriel's right about him - he needs to get laid. Badly.


	13. Bring the Funk

**Summary for the Chapter:**

> Castiel's in a funk. Something's got to be done.

Another week goes buy. More than. Eight days of sullen, eight days of moody and irate. Castiel wearing out his welcome in board meetings, in family gatherings. Finding excuses to go home, stay home. Cooped up in top-shelf penthouse on the island, magnificent view of the Hudson and all those lights that burn on the water. Burn for other people, lucky enough to have lives to live and someone waiting for them, somewhere.

Not that Cas would ever be really content with a life like that. He doesn't like being tied down, never has. Spent too much of his ridiculously long life following orders. His father, his brothers. Anyone a head above him. His loyalty to his family and sense of duty was all fine and well when he was young but for the last few years he's felt his life, his youth, slipped away from him. Wasted in their service. So, no. He won't be hitching his wagon to anyone's star. He wants a life that belongs to him.

And, yet.

Castiel is lonely. Didn't realize how bad it was, until now. He tries to push the feeling away. Work it out in the ring or fuck it away with whatever pretty, little thing just happens to be available. He reads. He works. He goes on long, stupidly expensive vacations just to clear his head. It sounds cliche but Cas feels different, like he's someone new, in Paris. In China. Reinvented in an English morning or a busy Russian street. New York, though. He can't stay away from her and, ever since that party, he hasn't been able to leave.

"You're looking somber." Anna's voice is softer than usual, not wanting to shock her brother out of the sad and lonely with a corporate tone. It's still there, though. She's not good at comfort.

Castiel finishes a sip of whatever's in that highball glass ( it's fizzy, like Sprite. Probably is Sprite ) and rests the glass on the massive, stone balcony's edge. He's been there, like this, leaning against the rail on folded arms and staring out at the harbor since the sun still chalked pink and yellow across the horizon. It's faded, now. Castiel can barely see it. He doesn't look over at Anna, vaguely wondering how long she's been here and how she managed to get in, but he doesn't ignore her, either, "Not now." but, kindly, "Please."

She half-rolls her eyes, reaches out to take his drink from him. Round ice cube and all, who does he think he's fooling? Takes a sip, "I know, it's not a good time." and sighs, "It never is, Castiel." For all the coldness and distance in her brother's voice, in his expression, no one knows him quite like she does, having worked under him in his office for the past several years. Trying to make a name for herself, climbing out from beneath the Shurley boys. She knows how he takes his coffee, she knows the difference between an irritated Castiel and one that might knock your teeth down your throat. He's more her brother, now, than he ever was in their life before all this. Her hand finds his, resting a warm palm over his wrist, "Don't shoo me away, I fucking hate it when you do that. And, I'm worried about you, Cas. Ever since your birthday you've been..." she sighs, again, and slowly lets him go and slides his mock highball in front of him.

Only, Castiel catches her hand, rests his atop, "I know. It's not my intention to be... difficult. I'm having a... a..."

"Crisis?" she offers, along with the offer of a smug little smirk. Anna really does let him go, now, and turns her back on the city. Leans back against the stone balcony enclosure, "Is it that guy? The one you were talking to... the one who left with Charlie?"

"Anna, do you know something?" alright, Cas already knows what he's about to do is stupid. He knows the rest of their siblings aren't taking too kindly to Anna and her budding relationship with the elfish little redhead who's still under contract with Celestial. He barely cares, though. He wants to know more about Dean. Even a last name would be something. Castiel finally turns towards his sister, fast enough to accidentally chuck the highball glass off the balcony. They hear it break, a dog bark, and someone yell obscenities but he doesn't pay it any attention.

If the look on Anna's face is anything to go by, Cas just might crawl out of this funk sooner, rather than later.


End file.
